WO2022019498A1 - Composition de peinture par électrodéposition - Google Patents

Composition de peinture par électrodéposition Download PDF

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Publication number
WO2022019498A1
WO2022019498A1 PCT/KR2021/007967 KR2021007967W WO2022019498A1 WO 2022019498 A1 WO2022019498 A1 WO 2022019498A1 KR 2021007967 W KR2021007967 W KR 2021007967W WO 2022019498 A1 WO2022019498 A1 WO 2022019498A1
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Prior art keywords
epoxy resin
epoxy
weight
composition
parts
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Ceased
Application number
PCT/KR2021/007967
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English (en)
Korean (ko)
Inventor
이규상
김효정
도경해
최재일
김성민
김건태
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KCC Corp
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KCC Corp
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Publication date
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Priority to CN202180029788.7A priority Critical patent/CN115702224B/zh
Publication of WO2022019498A1 publication Critical patent/WO2022019498A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08—Anti-corrosive paints

Definitions

  • the present invention relates to an electrodeposition coating composition capable of forming a coating film having excellent storage stability, filterability and weather resistance, and excellent rust prevention properties at edges.
  • the multi-layer coating is generally formed by applying electrodeposition coating, intermediate coating, top coating, and clear coating to the car body that has undergone a pretreatment process.
  • the electrodeposition coating is a coating method in which a conductor is immersed in an electrodeposition coating solution and a coating film is electrically deposited on the surface of the conductor through an electric current between the conductor and the counter electrode.
  • Epoxy type and acrylic type are mainly used as paints used for this electrodeposition coating, and the epoxy type is mainly applied in the coating specifications that require high corrosion resistance, and the acrylic type is mainly applied in the coating specifications that require weather resistance and appearance characteristics. have.
  • Patent Document 1 discloses polyoxyalkylene amine; glycidoxy alkyl alkoxy silanes; and a semi-porous agent that is an additive comprising a reaction product of a glycidyl compound.
  • the composition of Patent Document 1 has excellent edge coverage, but lacks storage stability and lacks filterability.
  • An object of the present invention is to provide an electrodeposition coating composition capable of forming a coating film having excellent weather resistance and excellent edge rust prevention, and excellent storage stability and filterability.
  • the present invention comprises a resin, a curing agent and a cationic water dispersion additive,
  • the cationic water dispersion additive is prepared from an additive composition comprising a first epoxy resin, a second epoxy resin, and an amine group-containing alkoxysilane,
  • It provides an electrodeposition coating composition
  • the first epoxy resin and the second epoxy resin in a weight ratio of 1:1 to 5:1.
  • the electrodeposition coating composition according to the present invention can form a coating film having excellent storage stability and filterability, excellent weather resistance, and excellent edge rust prevention.
  • the functional group such as 'content of unreacted NCO (NCO%)' may be measured by a method well known in the art, for example, may be a value measured by titration or the like.
  • the electrodeposition coating composition according to the present invention includes a resin, a curing agent, and a cationic water dispersion additive.
  • the resin is the subject of the electrodeposition coating composition, and serves to control the properties of the prepared coating film.
  • the resin is not particularly limited as long as it is a resin applicable as a general electrodeposition paint, and may include, for example, an epoxy resin.
  • the resin may be a bisphenol-type epoxy resin, and the bisphenol-type epoxy resin may be, for example, a bisphenol A-type epoxy resin.
  • the resin may be included in the composition in an amount of 5 to 30 parts by weight, or 10 to 25 parts by weight based on 5 to 30 parts by weight of the curing agent.
  • the content of the resin is less than the above content, the rust prevention property of the composition is insufficient, and when the content exceeds the above content, the problem of insufficient impact resistance of the prepared coating film may occur.
  • the curing agent performs a crosslinking reaction with the resin to cure the composition.
  • the curing agent may be an isocyanate resin, and the isocyanate resin is not particularly limited as long as it is a curing agent commonly used in paints.
  • the isocyanate resin may be, for example, aromatic isocyanate and alicyclic isocyanate, and when the aromatic isocyanate is exposed to UV, decomposition of the double bond of the aromatic ring may occur and weather resistance may be reduced. Therefore, it is preferably an alicyclic isocyanate.
  • the alicyclic isocyanate is, for example, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl cyclohexane (isophorone diisocyanate, IPDI), 1,4-diisocyanato-3, 3,5-trimethylcyclohexane, 1,3-diisocyanato-2-methylcyclohexane, 1,3-diisocyanato-4-methylcyclohexane, 1-isocyanato-1-methyl-4(3) -isocyanatomethyl cyclohexane, 2,4'- or 4,4'-diisocyanatodicyclohexylmethane, 1,3- or 1,4-bis(isocyanatomethyl)cyclohexane, 4,4' -diisocyanato3,3'-dimethyl dicyclohexylmethane, 4,4'-diisocyanato-3,3',5,5'-tetramethyl dicyclo
  • the isocyanate resin may have an end blocked with a blocking agent.
  • the blocking agent stabilizes the terminal isocyanate group to a specific temperature, and when it exceeds a specific temperature, it is dissociated from the isocyanate group to control the reactivity.
  • the blocking agent is, for example, diethylmalonate, dimethylpyrazole, cyclohexanone oxime, oxime compounds such as methylethyl ketoxime, lactam compounds such as ⁇ -caprolactam and ⁇ -butyrolactam, methanol, It may be an alcohol-based compound such as ethanol.
  • the curing agent may be included in the composition in an amount of 5 to 30 parts by weight, or 10 to 20 parts by weight based on 5 to 30 parts by weight of the resin.
  • the content of the curing agent is less than the above content, a problem of poor curability of the composition may occur.
  • the cationic water dispersion additive controls the flowability at the edge of the composition when forming the coating film, thereby improving the edge coverage and the coating film ascending property.
  • the cationic water dispersion additive is prepared from an additive composition comprising a first epoxy resin, a second epoxy resin, and an amine group-containing alkoxysilane.
  • the additive composition may include the first epoxy resin and the second epoxy resin in a weight ratio of 1:1 to 5:1, or 2:1 to 4:1 by weight.
  • the weight ratio of the first epoxy resin and the second epoxy resin is less than 1:1, that is, when a small amount of the first epoxy resin is included than the second epoxy resin, the edge coating film riseability of the composition is insufficient, and exceeds 5:1; That is, when the first epoxy resin is included in excess based on the second epoxy resin, the resin synthesis stability may be insufficient.
  • the epoxy resin (total amount of the first epoxy resin and the second epoxy resin) and the amine group-containing alkoxysilane may be included in a weight ratio of 5:1 to 1:1, or 3:1 to 1:1 by weight.
  • the weight ratio of the epoxy resin to the amine group-containing alkoxysilane is less than the above range, that is, when a small amount of the epoxy resin is included than the amine group-containing alkoxysilane, there is a problem of re-dissolution of the electrodeposition coating film due to an excess of unreacted amine, exceeding the above range That is, when an excessive amount of the epoxy resin is included, the storage stability of the additive may be insufficient due to an increase in the molecular weight of the prepared cationic water dispersion additive.
  • the first epoxy resin has a lower epoxy group content and a greater viscosity at 25° C. than the second epoxy resin.
  • the first epoxy resin has an epoxy group content of 300 to 2,000 mmol/kg or 500 to 1,100 mmol/kg lower than that of the second epoxy resin, and a viscosity at 25° C. of 40 to 75 mPa ⁇ s or 50 to 70 mPa ⁇ s can be large.
  • the first epoxy resin may have an epoxy group content of 2,500 to 3,500 mmol/kg, or 2,900 to 3,300 mmol/kg.
  • the epoxy group content of the first epoxy resin is less than the above range, the gloss of the coating film is lowered, and when it exceeds the above range, a problem of insufficient edge coverage of the composition may occur.
  • the first epoxy resin may have a viscosity at 25° C. of 50 to 80 mPa ⁇ s, or 55 to 70 mPa ⁇ s.
  • the viscosity at 25° C. of the first epoxy resin is less than the above range, the edge coverage of the composition is reduced, and when it exceeds the above range, the gloss of the coating film may be reduced.
  • the first epoxy resin may have an epoxy equivalent of 250 to 400 g/eq, or 300 to 350 g/eq.
  • the epoxy equivalent of the first epoxy resin is less than the above range, the gloss of the coating film is lowered, and when it exceeds the above range, edge coverage of the composition may be reduced.
  • the second epoxy resin may have an epoxy group content of 3,800 to 4,500 mmol/kg, or 4,000 to 4,300 mmol/kg.
  • the epoxy group content of the second epoxy resin is less than the above range, a problem occurs in the synthetic stability of the additive, and when it exceeds the above range, edge coverage of the composition may be reduced.
  • the second epoxy resin may have a viscosity at 25°C of 3 to 15 mPa ⁇ s, or 5 to 10 mPa ⁇ s.
  • the viscosity at 25° C. of the second epoxy resin is less than the above range, the gloss of the prepared coating film is reduced, and when it exceeds the above range, edge coverage of the electrodeposition coating composition may be reduced.
  • the second epoxy resin may have an epoxy equivalent of 200 to 280 g/eq, or 220 to 260 g/eq.
  • the epoxy equivalent of the second epoxy resin is less than the above range, the reaction rate of the composition increases and the workability of the composition is insufficient, and when it exceeds the above range, a problem of lowering purity may occur.
  • the amine group-containing alkoxysilane reacts with the epoxy group of the epoxy resin to form a cationic resin, and forms silanol from the resin. plays a role in controlling
  • the amine group-containing alkoxysilane may be represented by the following formula (1).
  • R 1 is a substituted or unsubstituted C 1 to C 10 alkylene group
  • R 2 is a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms.
  • R 1 may be a substituted or unsubstituted C 1 to C 5 alkylene group
  • R 2 may be a substituted or unsubstituted C 1 to C 5 alkoxy group.
  • the alkylene group and the alkoxy group may be linear or branched.
  • the alkylene refers to a branched or straight-chain or cyclic divalent radical derived by the removal of one hydrogen atom from a carbon atom of an alkyl group.
  • the alkylene is methylene (-CH2-), 1,1-ethylene (-CH(CH3)-), 1,2-ethylene (-CH2CH2-), 1,1-propylene (-CH(CH2CH3) )-), 1,2-propylene (-CH2CH(CH3)-), 1,3-propylene (-CH2CH2CH2-), 1,4-butylene (-CH2CH2CH2CH2-), 2,4-butylene (-CH2 (CH3)CH2CH2-), and the like, but is not limited thereto.
  • the cationic water dispersion additive may be a silane-modified epoxy resin containing a silanol group.
  • the cationic water dispersion additive has a solid content of 20 to 30% by weight or 23 to 27% by weight, a degree of neutralization of 10 to 40 mmol/100g or 15 to 35 mmol/100g, and a viscosity at 25°C It may be 10 to 100 cps or 30 to 80 cps.
  • the edge coverage of the composition is lowered, and when it exceeds the above range, the viscosity of the composition is increased and storage properties are lowered.
  • the neutralization degree of the cationic water dispersion additive is less than the above range, the storability of the composition is insufficient, and when it exceeds the above range, the problem of insufficient storability of the composition may occur.
  • the viscosity of the cationic water dispersion additive is less than the above range, edge coverage of the composition is lowered, and when it exceeds the above range, a problem of insufficient storability of the composition may occur.
  • the cationic water dispersion additive may be included in the composition in an amount of 3 to 15 parts by weight, or 5 to 10 parts by weight based on 5 to 30 parts by weight of the resin.
  • content of the cationic water dispersion additive is less than the above content, edge coverage of the composition is lowered, and when the content exceeds the above content, the appearance characteristics and gloss of the prepared coating film may be deteriorated.
  • the electrodeposition paint composition may further include at least one additive selected from the group consisting of an amine compound, a solvent, a neutralizer, an antifoaming agent, an oil removal agent, and a flow control agent.
  • the additives are not particularly limited as long as they can be used in the general electrodeposition coating composition.
  • the electrodeposition coating composition according to the present invention as described above can form a coating film having excellent storage stability and filterability, excellent weather resistance, and excellent edge rust prevention.
  • 112 parts by weight of a first epoxy resin in a reaction vessel (manufacturer: Dow Chemical, product name: DER 732, epoxy content: 3,130 mmol/kg, viscosity at 25°C: 65 ⁇ 5 mPa ⁇ s, epoxy equivalent: 320 g/eq), 36 parts by weight of a second epoxy resin (manufacturer: Hexion, product name: Cardura E-10P, epoxy content: 4,170 mmol/kg, viscosity at 25°C: 7 mPa s, epoxy equivalent: 240 g/eq), 110 parts by weight of an amine group Containing alkoxysilane (manufacturer: Momentive, product name: Silquest A-1100, gamma-aminopropyltriethoxy silane) and 120 parts by weight of isopropyl alcohol were added.
  • a cationic water dispersion additive was prepared in the same manner as in Synthesis Example 3, except that the content of each component was adjusted as shown in Table 1 below.
  • the epoxy equivalent is 1,000 g/eq or more
  • 24 parts by weight of the fourth epoxy resin (manufacturer: Kukdo Chemical, product name: YD-128, epoxy equivalent: 180 to 190 g/eq) is added to react the epoxy, and 19 parts by weight of lactic acid ( Aqueous solution having a concentration of 50% by volume) was added to neutralize, and 576 parts by weight of ionized water was gradually added dropwise to disperse in water to prepare a cationic water dispersion additive-7 having a solid content of 35% by weight and a degree of neutralization (MEQACID) of 25mmol/100g did
  • Part 13 the solvent corresponding to the content of Part 13 was vacuum recovered to obtain a resin reactant.
  • the first aqueous dispersion was carried out while putting the resin reactant into the dispersion tank containing parts 14 to 16, and after stirring for 1 hour, part 17 was added to adjust the viscosity. Thereafter, the temperature was adjusted to 45° C. or less, and part 18 was added to prepare an electrodeposition coating composition.
  • the physical properties of the prepared coating film were measured in the following manner, and the results are shown in Tables 5 and 6.
  • the 60° gloss of the coating was measured vertically and horizontally. At this time, it was determined that the higher the gloss value, the higher the gloss.
  • the number of transfers until the coating film was scratched was measured at 170°C and 175°C using a side sufficiently wetted with methyl isobutyl ketone (MIBK) solvent in the coating film.
  • MIBK methyl isobutyl ketone
  • the hardness of the coating film was measured using a Mitsubishi pencil according to MS652-05 and ISO15184.
  • the maximum hardness that does not damage the final coating film was measured using each of 3B, 2B, B, HB, F, H, 2H, and 3H pencils (3B, 2B, B, HB, F, H, 2H). , 3H: inferior ⁇ excellent).
  • Gloss change was confirmed based on Q-UVA Type 21 days according to ISO 11507. Based on the 60° gloss of the initial coating film before the weather resistance test, if the gloss change rate was less than 10%, it was evaluated as excellent, if it was 10% or more and less than 30%, it was evaluated as normal, and if it was 30% or more, it was evaluated as poor.
  • Specimens were prepared and exposed outdoors for 21 days, and gloss changes were confirmed based on the 60° gloss of the initial coating film before testing. When the gloss change rate was less than 10%, it was evaluated as excellent, when it was 10% or more and less than 30%, it was evaluated as normal, and when it was 30% or more, it was evaluated as poor.
  • the electrodeposition coating composition was coated on the edge portion of the blade (knife) as described above, and the coating film thickness of the edge portion of the blade (knife) was measured with an electron microscope.
  • the electrodeposition coating composition was applied to the punched specimen (manufacturer: Ever Steel) at 240V for 3 minutes, and the coating film thickness of the edge portion of the punched specimen was measured with an electron microscope.
  • the degree of passing of the electrodeposition paint compositions prepared in Examples and Comparative Examples was evaluated using a 100 mesh nylon sieve, and filter properties were evaluated with ⁇ (excellent), ⁇ (normal), and X (poor).
  • the filterability was evaluated in the same manner as described above after the composition was stored at 40° C. for 7 days.
  • compositions of Examples 1 to 5 have excellent filterability even after storage at 40° C. for 7 days, a small size of sieve residue, excellent coating film ascending properties, and physical properties of a coating film prepared therefrom It was excellent.
  • Comparative Example 2 using the cationic water dispersion additive of Synthesis Example 6 without the second epoxy resin and Comparative Example 3 using the cationic water dispersion additive of Synthesis Example 7 without the first epoxy resin were stored at 40° C. It lacked filterability and lacked weather resistance.
  • Comparative Example 5 using a silane-modified epoxy amine compound instead of the cationic water dispersion additive was poor in weather resistance.
  • the electrodeposition coating composition according to the present invention can form a coating film having excellent storage stability and filterability, excellent weather resistance, and excellent edge rust prevention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une composition de peinture par électrodéposition comprenant une résine, un durcisseur et un additif ayant des cations dispersés dans l'eau, l'additif étant produit à partir d'une composition d'additif comprenant une première résine époxyde, une seconde résine époxyde et un alcoxysilane contenant un groupe amine, la première résine époxyde et la seconde résine époxyde étant présentes dans un rapport pondéral compris entre 1:1 et 5:1.
PCT/KR2021/007967 2020-07-22 2021-06-24 Composition de peinture par électrodéposition Ceased WO2022019498A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202180029788.7A CN115702224B (zh) 2020-07-22 2021-06-24 电沉积涂料组合物

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KR1020200090826A KR102889295B1 (ko) 2020-07-22 2020-07-22 전착도료 조성물
KR10-2020-0090826 2020-07-22

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